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Reactivity of antipyrine and haloantipyrines in Pd-catalyzed C–H bond arylations

Abstract : We reported herein the Pd-catalyzed direct arylation of antipyrine using Pd(OAc)2 as catalyst associated with KOAc as inexpensive base. In most cases, diethyl carbonate was used a sustainable solvent. The reaction tolerated a wide range of functional groups on the aryl bromide partners (e.g., nitrile, nitro, chloro, fluoro, formyl, acetyl, propionyl, benzoyl, ester, methyl, methoxy). In addition, some nitrogen-containing heteroaryl bromides were also efficiently coupled with antipyrine. We also demonstrated that in contrast to 4-bromoantipyrine, 4-iodoantipyrine could be employed as an efficient heteroaryl source in Pd-catalyzed C–H bond arylation of 5-membered ring heteroarenes.
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A. Sasmal, J.K. Bera, H. Doucet, Jean-François Soulé. Reactivity of antipyrine and haloantipyrines in Pd-catalyzed C–H bond arylations. Tetrahedron Letters, Elsevier, 2020, 61 (17), pp.151798. ⟨10.1016/j.tetlet.2020.151798⟩. ⟨hal-02569945⟩

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